Derivatives of 4:4&#39;-diaminodiphenylsulphones and process of making same



Patented May 22, 1945 UNITED STATES PATENT OFFICE DERIVATIVES OF 4:4'-DIA1\IINODIPHENY L- SULPHONES AND PROCESS OF MAKING SAME , Max Hartman and Jean Druey, Riehen, Switzerland, assignors to Cilia Pharmaceutical Products, Incorporated, Summit, N. J., a corporation of New Jersey No Drawing. Application May 24, .1943, Serial No. 488,258. In Switzerland June 6, 1942 7 Claims.

tives of 4:4'-diaminodiphenylsulphone can be obtained by allowing 4:4-diaminodiphenylsulphones which contain at least one unsubstituted amino group to react with acetaldehyde-disul-' phonic acids or their derivatives. Particularly valuable compounds are obtained if 4:4'-diaminodiphenylsulphones, in which an amino group is substituted, e. g. with an acid radical such as the acetic acid or the carbamic acid radical, are used as starting products.

Acetaldehyde-disulphonic acids or their derivatives or salts, respectively, e. g. acetaldehydedisulphonic acidsodium, bromaceta1dehyde-disulphonic acid sodium, etc., are used for the reaction, which is carried out in a known manner. The sulphones are reacted, for example, with the disodium salt of acetaldehyde-disulphonic acid in water at increased temperature and the sodium salts then isolated in the usual way.

The compounds obtained by the present process are intended for therapeutic use.

i Th following examples illustrate the invention, but are notto be regarded as limiting it in any way, the parts being by weight:

Example 1 uct is obtained which has theformula:

Yield about as parts. The product is fairly easily soluble in water.

Example 2 82 parts of the barium salt of acetaldehydedisulphonic acid are dissolved in 1000 parts of hot water, and 30 parts of dry sodium sulphate added. The precipitated barium sulphate is separated oflf and thesolution heated on a water bath with 24 parts of p:p'-diaminodiphenyl-su1- phone until the latter is all dissolved. The water is then distilled 01f in vacuo. The residual tetrasodium salt of the formula:

crytallizes out after standing for some time.

In a similar way other salts, e. g. the calcium salt or salts with organic bases can be obtained.

What we claim is: 1. A therapeutically active compound selected from the group consisting of the 4:4-diaminodiphenylsulphones, in which at least one amino group is substituted by a flus-disulphoethylidene group, and their salts.

2. A therapeutically active 4-amino-4'-acylaminodiphenylsulphone, in which the amino group in 4-position is substituted by a pus-disulphoethylidene group.

3. A therapeutically active salt of a 4-aminoiacylamino-diphenylsulphone, in which the amimo group in ii-position is substituted by a fizfi-disulphoethylidene group. i

4. The therapeutically active compound of the formula 5. A process for the manufacture of a therapeutically active derivative of i:4-diaminodiphenylsulphone, which comprises causing a 4:4-

diaminodiphenylsulphone, which contains at least aminolacylamino-diphenylsulphone to react with a member of the group consisting of bromacetaldehyde disulphonic acid, acetaldehyde disulphonic acid, and their salts.

I. A process for the manufacture of a, therapeutically active derivative of 4:4'-diaminodiphenylsulphone, which comprises causing a 4:4- diaminodiphenylsulphone, which contains at least one unsubstituted amino group, to react with the disodium salt of acetaldehyde disulphonic acid.

MAX HARTMANN. JEAN DRUEY. 

